Perylene-conjugated pyrrole polyamide as a sequence-specific fluorescent probe.
Perylene-conjugated pyrrole (Py)-polyamide 2 was designed and synthesized using the Fmoc solid-phase synthesis and a subsequent Sonogashira coupling reaction with 3-bromoperylene. Interestingly, conjugate 2 did not luminesce in water at 313 nm irradiation but was turned on in the presence of target double-stranded (ds) DNA, and showed strong emission with increasing DNA concentration, in particularly, by the binding to the target telomere sequences through heterodimer formation with partner 3. Importantly, the excitation spectrum of 2 clearly indicates that the Py and Imidazole (Im) moieties in the polyamide effectively sensitize the perylene moiety to give rise to fluorescence emission. Energy transfer would occur from the Py moiety to the perylene. Thus, screening of perylene-conjugates will allow us to develop a novel "molecular light switch" with sequence-specificity.
Fujimoto
Jun
J
Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo, Kyoto 606-8502, Japan.
Bando
Toshikazu
T
Minoshima
Masafumi
M
Kashiwazaki
Gengo
G
Nishijima
Shigeki
S
Shinohara
Ken-ichi
K
Sugiyama
Hiroshi
H
D001483:Base Sequence; D004247:DNA / Q000737:chemistry / Q000235:genetics; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D009757:Nylons / Q000138:chemical synthesis / Q000737:chemistry*; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D016615:Telomere / Q000737:chemistry
D005456:Fluorescent Dyes; D009757:Nylons; D010569:Perylene; D004247:DNA